CAS 129618-40-2|@nevirapine|2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one|11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E...

General Information

Structure

Molecular Formula

C₁₅H₁₄N₄O

Molecular Mass

266.29786

Exact Mass

266.11676109

Charge

InChI

InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)

InChIKey

NQDJXKOVJZTUJA-UHFFFAOYSA-N

Canonic Smiles

Cc1ccnc2c1[nH]c(=O)c1c(n2C2CC2)nccc1

Isomeric Smiles

O=c1[nH]c2c(n(C3CC3)c3ncccc13)nccc2C

Calculated Properties

JChem

Acid pKa

10.371185

H Acceptors

H Donor

LogD (pH = 5.5)

2.3533716

LogD (pH = 7.4)

2.480226

Log P

2.4880428

Molar Refractivity

77.482

Polarizability

28.112658

Polar Surface Area

58.12

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.75

LOG S

-3.41

Solubility (Water)

1.05e-01 g/l

Data Source

Names and Identifiers

IUPAC Traditional name

@nevirapine nevirapine 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

IUPAC name

2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one

Synonyms

11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONEViramune11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-oneBI-RG 587NevirapineNevirapine11-cyclopropyl-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-oneNVPNEVNevarapine11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2’,3’-e][1,4]diazepin-6-oneNSC 6415302-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

Brand Name

Viramune

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem SID

PubChem CID

Registration numbers

Properties

Product Information

Salt Data

Free Base

Purity

≥98% (HPLC)

95%

Empirical Formula (Hill Notation)

C15H14N4O

Certificate of Analysis

Download link

Application(s)

Virucide

Used to treat HIV-1 infection and AIDS

Safety Information

Pharmacology Properties

Mechanism of Action

Non-nucleoside reverse transcriptase inhibitor (NNRTI)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00238

Drug Groups

approved

Description

A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]

Indication

For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

Pharmacology

Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Nevirapine is, in general, only prescribed after the immune system has declined and infections have become evident. It is always taken with at least one other HIV medication such as Retrovir or Videx. The virus can develop resistance to nevirapine if the drug is taken alone, although even if used properly, nevirapine is effective for only a limited time.

Toxicity

Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease.

Affected Organisms

Human Immunodeficiency Virus

Biotransformation

Hepatic. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites.

Absorption

90% (absolute bioavailability 93 ± 9%)

Half Life

45 hours

Protein Binding

60%

Elimination

Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (<5%) of the radioactivity in urine (representing <3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.

Distribution

* 1.21 ± 0.09 L/kg

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

DB08311

Drug information: experimental

Selleck Chemicals

S1742

Research Area: Infection
Biological Activity:
Nevirapine(Viramune) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS.[1] Nevirapine is not effective against HIV-2, as the pocket of the HIV-2 reverse transcriptase has a different structure, which confers intrinsic resistance to the NNRTI class. [1]

Sigma Aldrich

SML0097

Biochem/physiol Actions
Nevirapine is an allosteric, non-nucleoside inhibitor of HIV reverse transcriptase (NNRTI). The Ki for inhibition of wild-type RT by Nevirapine is 200 nM.

TRC

N391275

A potent (IC50=84nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase. Antiviral.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Nevirapine

• Hargrave, K.D., et al.: J. Med. Chem., 34, 2231 (1991)

• Guay, L.A., et al.: Lancet, 354, 795 (1991)

• Cheeseman, S.H., et al.: Antimicrob. Agents Chemother., 37, 178 (1991)

• Koup, R.A. et al., J. Infect. Dis., 1991, 163, 966, (pharmacol)

• Grob, P.M. et al., AIDS Res. Hum. Retroviruses, 1992, 8, 145, (pharmacol, rev)

• Pedersen, O.S. et al., Synthesis, 2000, 479-495, (rev)

• Hargrave, K.D. et al., J. Med. Chem., 1991, 34, 2231, (synth, pharmacol)

• Skoog, M.T. et al., Med. Res. Rev., 1992, 12, 27, (rev)

• Eur. Pat., 1991, Boehringer Ingelheim, 429 987; CA, 115, 114559n, (synth, pharmacol)

• Merluzzi, V.J. et al., Adv. Exp. Med. Biol., 1992, 312, 89, (rev)

• Mui, P.W. et al., J. Med. Chem., 1992, 35, 201, (cryst struct)

• Grozinger, K.G. et al., J. Het. Chem., 1995, 32, 259, (synth)

• Cohen, K.A. et al., J. Biol. Chem., 1991, 266, 14670, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1393

• Merluzzi, V.J. et al., Science (Washington, D.C.), 1990, 250, 1411, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

@nevirapine nevirapine 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one

IUPAC name

Synonyms

Brand Name

Viramune

Registration numbers

CAS Number

MDL Number

PubChem SID

PubChem CID

Properties

Product Information

Salt Data

Free Base

Purity

≥98% (HPLC)

95%

Empirical Formula (Hill Notation)

C15H14N4O

Certificate of Analysis

Download link

Application(s)

Virucide

Used to treat HIV-1 infection and AIDS

Safety Information

Pharmacology Properties

Mechanism of Action

Non-nucleoside reverse transcriptase inhibitor (NNRTI)

Molecule Details

DrugBank

DB00238

Drug Groups

approved

Description

A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]

Indication

For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

Pharmacology

Toxicity

Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease.

Affected Organisms

Human Immunodeficiency Virus

Biotransformation

Absorption

90% (absolute bioavailability 93 ± 9%)

Half Life

45 hours

Protein Binding

60%

Elimination

Distribution

* 1.21 ± 0.09 L/kg

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

DB08311

Drug information: experimental

Selleck Chemicals

S1742

Sigma Aldrich

SML0097

Biochem/physiol Actions
Nevirapine is an allosteric, non-nucleoside inhibitor of HIV reverse transcriptase (NNRTI). The Ki for inhibition of wild-type RT by Nevirapine is 200 nM.

TRC

N391275

A potent (IC50=84nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase. Antiviral.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Nevirapine

• Hargrave, K.D., et al.: J. Med. Chem., 34, 2231 (1991)

• Guay, L.A., et al.: Lancet, 354, 795 (1991)

• Cheeseman, S.H., et al.: Antimicrob. Agents Chemother., 37, 178 (1991)

• Koup, R.A. et al., J. Infect. Dis., 1991, 163, 966, (pharmacol)

• Grob, P.M. et al., AIDS Res. Hum. Retroviruses, 1992, 8, 145, (pharmacol, rev)

• Pedersen, O.S. et al., Synthesis, 2000, 479-495, (rev)

• Hargrave, K.D. et al., J. Med. Chem., 1991, 34, 2231, (synth, pharmacol)

• Skoog, M.T. et al., Med. Res. Rev., 1992, 12, 27, (rev)

• Eur. Pat., 1991, Boehringer Ingelheim, 429 987; CA, 115, 114559n, (synth, pharmacol)

• Merluzzi, V.J. et al., Adv. Exp. Med. Biol., 1992, 312, 89, (rev)

• Mui, P.W. et al., J. Med. Chem., 1992, 35, 201, (cryst struct)

• Grozinger, K.G. et al., J. Het. Chem., 1995, 32, 259, (synth)

• Cohen, K.A. et al., J. Biol. Chem., 1991, 266, 14670, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1393

• Merluzzi, V.J. et al., Science (Washington, D.C.), 1990, 250, 1411, (pharmacol)

Bioactivity

PubChem BioAssay

Molecule

ID:123